Trump has been UP and Trump has been DOWN. Fact is he has probably had more complex experience than anyone now running or planning to run for President. Here is a long meaty detailed article from 1990 in Fortune when he ran into difficulties for reasons ranging from overoptimism to economic problems in Japan, New York, and Massachusetts. He had already shown his ability to make money, now he had to show how to avoid loosing it all.
http://archive.fortune.com/magazines/fortune/fortune_archive/1990/08/13/73899/index.htm
Now an update on bankruptcies: http://www.vanityfair.com/news/2015/06/donald-trump-companies-bankruptcy-atlantic-city
One article I read pointed out that all the Atlantic City casinos/hotels could have done a lot better if they had paid more attention to upgrading the overall economy and look of AC instead of totally neglecting it for short range benefit of their bottom lines. This more recent information regarding Trump’s success has a decidedly liberal slant, which doesn’t necessarily mean it is wrong. Judge for yourself.
This link does a good job of outlining Trump’s recovery from his 1990 challenges up to 2002 successes. http://www.encyclopedia.com/topic/Donald_Trump.aspx
Finally a word about Trump’s NET WORTH. He has declared that it is $10 billion. Other reputable sources are suggesting closer to $4 billion. Still plenty rich and far more than Hillary’s $20 million or Walker’s $75,000. Here is a link touching on net worth and including other links to the Trump wealth story.